


Devil May Care

by becsbunker



Category: Supernatural
Genre: F/M, Mobster Jensen Ackles
Language: English
Status: Completed
Published: 2020-01-23
Updated: 2020-01-23
Packaged: 2021-02-26 22:38:28
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,213
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22373602
Author URL: https://archiveofourown.org/users/becsbunker/pseuds/becsbunker
Summary: Summary: It’s been 6 years since you were forced to leave Dean’s life, but even that time apart hasn’t changed your feelings for him.Warnings: mobster au, angst, threats, mentions of a car accident + injuries and kidney transplant, language, light fluff, brief smut mention
Relationships: Dean Winchester & You, Dean Winchester/You, Dean/You
Kudos: 20





	Devil May Care

Even stepping out of your car and seeing the neon lit 'Roadhouse' sign outside the bar had your nerves on edge. Maybe you should just turn back now, act like you never intended to see Dean Winchester in the first place. 

Dean and his brother ran a mob gang, they were famous for being one of the most notorious families in the country. You used to be a part of that. Or so they thought. Up until it turned out you were really an undercover FBI agent, sent in by your boss in the crime unit. 

At first, you were thrilled by the opportunity to use your skills and to grow your career in the bureau. Taking down a couple of famous mobsters was definitely one way to boost a resume. You were all set on following your goal, finding the evidence that would put the Winchesters away for a very long time. But nothing and no one could prepare you for falling head over heels for Dean.

Six years had passed since the fateful night Dean had discovered the truth. When you first started undercover at the roadhouse you're biggest worry was getting shot if anyone found out your real job, but in the end, Dean Winchesters broken heart is what killed you the most. 

There was an upbeat bass from the speakers as you stepped inside, people drinking and dancing, clearly enjoying the atmosphere and booze. 

The place seemed to have barely changed, just a few modernisations here and there. You didn't recognise many faces, which you were thankful for. The last thing you needed was to get into a row with anyone who knew who you were, and what you did. 

"You got some nerve showing up here." 

Great. 

You turned to the sound of the female voice, trying to hide your distaste at seeing Lisa stood there in a dress that barely covered anything up.

"I see you crawled back into the woodwork," you muttered. "Is your boss in?" 

Lisa scoffed. "Like he's ever going to want to see you." She surveyed you up and down with a look of disgust. "He's better off without you. Always was." 

You hid how much that comment stung well. Years and years of being a Fed helped with that. 

"Are you going to tell him I'm here or do I have to pay you first like your clients do?" You replied, satisfied by the scowl on Lisa's face as she stormed off to get Dean. 

The moment he stepped out of that door and into the main bar, you felt your pulse race and stomach drop. 

It had been six years, but he had aged like fine wine. If anything, he looked even more handsome than you remember - how that was possible was beyond you. 

Dean walked over to you, oozing authority to everyone else around, but you knew he was probably feeling a hundred and one other things after seeing you again. 

The closer he got, the more you wanted to turn and run. You should feel fear after what you did to him and Sam, how you betrayed them, but all you could think about was being in Dean's arms again. You couldn't let yourself think like that. 

When he stopped in front of you, you could see the scruff over his face and crows feet by his eyes. But still he was impossibly gorgeous. You could tell he was tired, knowing from experience that this life of his wasn't one without its stresses. You felt guilty as hell for your part in that. 

"Do you want a drink?" His voice was deeper than you remember, and you desperately tried to focus on anything else other than the way it made your knees feel weak. 

"I don't drink anymore." You were relieved by how normal you managed to get your voice to sound. Out of all the scenarios that ran through your head about coming here to ask Dean for help, you didn't prepare yourself for how much being around him would still affect you. 

Dean's eyebrow raised slightly. "A water then?" 

"Yeah, please." 

He called one of the staff over for the drink order before leading you through the door and the hallway until you reached his office. 

Unlike the main bar, everything in the office was exactly the same as before. Including the initials you'd carved into the wooden desk together. 

"Have a seat," Dean gestured to the couch at the side of the room. You tried to block out the memories of the times you'd had sex on that same couch, and multiple other pieces of furniture in this place. 

"I'm all right," you said, opting to stay standing. "Dean, the reason I'm here is -" 

"Because you owe Bela money and you need me to bail you out." 

Your eyes widened. "How - how do you know about that?" 

Dean rolled his eyes, casually sitting down on his chair and resting his feet up on the desk. "After you fucked me over, I've been keeping tabs," he told you. "I know you lost your job with the feds after burying all the evidence against me and my brother. I know you moved to Wisconsin. I know you were dating some accountant but you blew him off because he couldn't get it up. Am I missing anything?" 

Your surprise quickly turned to anger at the complete invasion of your privacy, of your life. "You've been fucking watching me all this time?" You snapped. "What? You've got nothing better to do? No people to terrorize, no hookers to fuck. What gives you the right?" 

Dean's jaw ticked and you saw the darkness flash across his eyes as he swung his legs so his feet were back on the floor before he stood up and strode over to you. 

"You," he growled, standing toe to toe with you. "You gave me the right when you first waltzed in here, pretended to care about my family, acted like you loved me. You tried to take my whole life from me. Everything I ever worked for. Forgive me if I find it fucking hard to trust you after that." 

You swallowed the lump in your throat, trying to fight the tears stinging your eyes. "Except I didn't take you or this fucking dynasty down, did I? I sacrificed my whole career because I fell in love with you." 

Dean scoffed. "You never loved me." 

"Yeah, I did. “You might not have been my first love but you were the love that made all others seem irrelevant” 

He was silent for a moment. A glint of that softness you'd seen all those years ago seemed to pass his face before a knock on the door made him step back. 

"What?" He called and you quickly wiped a hand over your face. 

"I brought your drinks," Lisa came in, hips swaying as she carried in the tray of drinks and placed it on the desk. 

"Thanks sweetheart," Dean said, going over and picking up his glass of whiskey to take a swig.

Just hearing that word leave his mouth for her made you feel sick to your stomach. 

Lisa glanced at you before looking at her boss, "is there anything else you need?" You knew what she was insinuating and it didn't help your mood in the slightest. 

"Come back in 20." 

Lisa practically beamed at Dean's reply before turning on her high heels and flaunting back out of the office. 

Clearly Dean noticed your irritation because he smirked as he handed you the glass of water. "You look like you might need this." 

You grit your teeth and took the glass, glaring at him. "So if you know everything already, I just need a loan. I'll pay you back the full amount at the beginning of next month." 

Dean clicked his tongue. "There’s just one thing that’s been bugging me. Why do you owe Bela money? I mean, she said it's because you stole an artifact and never returned it, but that's some lame story." 

You smiled slightly as you handed him back the glass without even taking a sip - not trusting that Lisa hadn't done something to it.

"Looks like you don't know everything. Can you help me or not?" 

"Give me the details of Bela's guys and I'll deal with it," Dean said, and even after all these years that authoritative tone had you secretly wanting to give him everything he ever wanted. But in the situation you were in, you knew you had to be the one calling the shots. You couldn't just let him hurt or kill the men who worked for Bela, you had to finish what you started. You had to pay her back. 

"No. I just need to borrow the money."

"Listen sweetheart, if you don't like the way I do things, go get a loan from a fucking bank - save us both the trouble."

That was enough to push you. "Fine. I will," you said, storming out and making sure the door slammed in your wake. 

  
~~~~~ 

" Charlie, is there anything else you might have missed?" 

"I'm not an amateur, Dean," the redhead huffed down the other end of the phone. "I searched everything to do with Y/N like you asked, except medical records." 

Dean frowned. "Then search her medical records." 

"Why?" 

"Because she owes Bela and I want to know why." 

There was a brief silence. 

"Boss, you know I love you," Charlie said. "But I don't remember you usually caring this much about the people you say you hate." 

There were many times Dean had the exact same thought. Hell, even Sam had mentioned it, but it always ended with Dean wanting to throw a punch. 

Of course he should hate you. The betrayal alone should have done that. But he hates himself more. He hates himself for not being able to stop loving you, even after all this time. Dean used to wonder if you ever felt like that, but after that reunion today, he knows you just might. 

Dean pinched the bridge of his nose. "Just search her medical records, OK? Get back to me as soon as." 

  
~~~

You didn't know why you thought going to Dean would help. Maybe you hoped it would have been that push you needed to tell him the truth. Tell him that you still loved him, that you were sorry. 

Seeing Dean again wasn't something you'd expected to happen. Sure, you'd thought about it more times than you could admit, but you never thought you'd actually see him again. 

Even when you were sick and in hospital 3 years ago after a car accident that resulted in kidney failure, you had thought about contacting him when the nurses asked. In the end, it was your brother, Matt, who was by your side every step of the way through the kidney transplant and your recovery. 

Your relationship with your brother wasn't it's best when he found out why you'd really left the FBI, why they had fired you, but all that seemed to disappear once he saw you lying in that hospital bed. 

After the accident, you worked on building up your relationship with Matt again, you openly told him about why you betrayed the bureau and how you saw that glimmer of love and kindness in Dean Winchester. He could tell that you had fallen for the notorious mobster and still felt that way even years later, and you could hardly argue with that. 

When you left the hospital, you moved to Wisconsin to live closer to Matt. It was a slow road to recovery, but once you were on your feet again- you found a job at a local library. It was part time and the furthest thing from being an agent or undercover in a mob family, but it gave you some stability. Some normality - for a while at least. 

With the medical expenses after your accident and the pain medication you still took to this day, bills added up and Matt became increasingly worried about you. That's what had pushed him to break into one of Bela's shops and steal the nearest thing he could find and sell on. He had no idea that she was a thief with contacts in other mobs who would do her dirty work for a fee. You'd found a way to contact her, promising you'd pay twice the amount of what Matt owed if she called off the men she'd hired. 

Being around Dean had taught you a lot, including how to get to people like Bela Talbot. It was clear she thought you wouldn't pay her back, but she agreed to give you time. 

Time that was quickly running out as you pulled up outside the bank. 

You got out of your car and headed straight for the entrance, confused when you found the door firmly locked. 

"What the fuck-" you stepped back, noticing the sign on the window. 

'The bank is closed due to a power cut. Sorry for any inconvenience.' 

"This is bullshit." You knocked hard on the door, hoping that anyone would answer. 

A familiar sound of a car engine rumbling nearby made you stop and turn, your face falling when you saw the classic 67 chevy and Dean in the driver's seat as he pulled up outside the bank. 

He rolled down the window, leaning his head out. "Come on, I'll give you a ride to the next town," he offered. 

You scoffed, crossing your arms over your chest. "I can drive myself." 

"Y/N, just get in the damn car. Please." The sincerity over his face made you falter in your plan to just get in your own car and drive off. 

With a sigh, you walked around to the passenger side and got in the car. You had to admit, you missed the impala. It was a beautiful car, one that was Dean's pride and joy. Although the inside didn't look half as clean as it used to. 

You noticed the empty wrappers and the bright pink bra in the backseat and scrunched up your nose in disgust. 

"Wow, still as classy as ever," you commented, focusing your attention back on the road ahead as Dean drove. 

He glanced over at you, a small smirk tugging at the corner of his lips. "I don't remember you complaining when we fucked in the backseat." 

"Shut up," you huffed, not wanting any more recollection of your time together. You didn't want him to see the effect it had on you. 

Dean's smile didn't falter as he watched the road. "Do you ever think about it?" 

"No." 

That made him roll his eyes. "Since you lost the badge, you've become a crappy liar," he scoffed, making you glare at him. 

"Yeah? Well I guess it takes one to know one." 

The tension was brewing with full steam as Dean's head snapped to you, "the hell is that supposed to mean?" 

"For one, it's kinda convenient that the only bank in town suddenly got a power cut when I needed to go there after talking to you - the one man who practically runs the whole of Lawrence," you deadpan. "Two, this is the route that goes to your place, not the next town."

Dean's frustration seeped away a little. "The feds must be kicking themselves for losing you," he muttered, flexing his fingers around the steering wheel.

And they're not the only ones, Dean thought silently. 

  
The rest of the ride was spent in silence, other than the cassette Dean had playing. You were surprised it even still worked. You remember the time Sam put an ipod jack in here and Dean threw it out of the window and drove over it. That was the same day he took you down to the lakes and you convinced him to go skinny dipping. Then you found a creative way to warm up afterwards before spending the night in the car. 

"What are you thinking about?" Dean asked as he pulled up outside his large house, clearly noticing the way you'd drifted off in thought and hadn't even realised you'd arrived. 

"Uh, just the lakes," you said, making Dean's eyebrow raise. He wasn't expecting that answer. The fact you even still thought of your time with him made his chest feel tight. 

You cleared your throat, making yourself concentrate on the reason you were even here in the first place. "Listen Dean, I don't have much time to pay Bela back. If this is just some sort of payback for what I did -" 

Dean snorted. "You think I'm gonna lock you up and throw away the key?" 

"No. But I know you're the reason the bank was closed." 

He sniffed, running a hand over the scruff on his face. "Come inside. I'll give you the money." Dean said, giving you no chance to ask anymore questions before he left the car. 

"I should've just gone to a bank in the first place," you mumbled to yourself, forcing yourself to get out of the impala and follow him inside the house. 

Just like Dean's office, the interior of the house was no different. Even for a mobster, it still felt like somewhat of a homely place. The home was where Dean kept his valuable possessions, like the photos of his parents and the ones where him and Sam were kids. All the mob business was done at the roadhouse, meaning Dean got the freedom of just living here with Sam and his wife, Jess. The house was originally just meant as a cover, a hideout, but to Dean it felt like home. 

You knew your way around the house from your time with the Winchesters. Knew each room and where every corridor led. 

That's how you realised Dean was leading you to his bedroom. Naturally you would have thought that he had an ulterior motive, but you knew that's where he kept the majority of his money. Under the floorboards beneath his bed. 

Stepping into his room brought a wave of memories and nostalgia. The way his body moved over you as you lay naked on the bed, the muscles of his back firm beneath your hands, the thrum of heat building inside you as the slick pull and push of his cock had you writhing under him. 

"Y/N," Dean's voice pulled you out of the thoughts. "I said how much money do you need?" 

You could feel how warm your cheeks were as you looked at him. "I, uh, 10 grand," you answered. "The artifact was worth 5, but I made a deal to give Bela double to make sure Matt was safe." 

"Matt? Your brother." 

Shit. 

A look of empathy and understanding covered Dean's face as he stepped closer, the hammering in your chest growing ten fold. 

"I got Charlie to look up your medical records after you left earlier. I figured there must be some reason you'd be stupid enough to deal with Bela. Now I know why. Your brother stole from her to pay for your medical bills." 

The overwhelming emotion had your eyes brimming with tears as you shoved roughly at his chest. "You had no right to do that! How dare you!" You yelled. 

Dean didn't stop you when you shoved at him, didn't even try to fight back. 

"Why didn't you tell me when you were in the hospital?" His voice actually sounded broken as he spoke, genuinely surprising you. 

"I - I wanted to, but I didn't think you would even care." 

"You thought I wouldn't care? Y/N, you could've died!" Dean argued. 

You shake your head, tears rolling down your cheeks. "When you threw me out, you told me you never wanted to see me again. Why would me almost dying change that?" 

His jaw tensed as he bit back tears. "Fuck you. Seriously. Fuck. You." 

Before you could even respond, Dean crashed his lips onto yours, his hands holding your face as he kissed you like you were his own lifeline.

You were stunned, frozen to the spot. Then the shock morphed into need, into want. You kissed him back, reminisced in the feel of his soft lips on yours, on the way his callus hands pressed against your skin, on the first move of his tongue against yours. 

It was fire and light and life all bursting into one. 

You didn't want to pull away, but you knew you had to. 

"Dean, wait - we should talk about everything," you parted with breathless words, placing your hands on his chest as he opened his eyes and looked at you with more light in his eyes than before. 

"There's things I need to say. There's a lot I want to tell you. But most importantly, I need you to know that I never meant to break your heart. Being in the FBI, getting assigned to go undercover, it felt like the push I needed in life," you admitted. "The unit I worked for, turns out it's just as corrupt as the people they are hunting down. I didn't realise that until I looked further into the way you run things, into the contacts you have. Then I got caught up in my feelings for you and I didn't want to fight that." 

You shake your head with a humourless laugh, "even now, I still can't fight the feelings I have for you. I love you. Out of everything that's happened, my biggest regret is hurting you. I am so sorry Dean.” 

He bit his lip, trying to process everything. What you were saying, how he was feeling. His life was a series of unknown things, the next deal, who they could trust, whether they’d even survive the week. The one thing he’d always been so sure of was his love for you. That had never changed. 

“Yeah, you hurt me. When I found out you were an undercover agent, I was angry. I felt like my whole world had caved in, but I wish I’d given you a chance - that I'd heard you out.” 

He let out a sigh, scratching the back of his neck before he continued, 

“The fact you got rid of all the incriminating evidence, I knew that somewhere along the line, you must've changed your mind about us. About me. That I wasn’t as much of a monster like you first thought. That maybe, you really had loved me as much as I love you. But my pride wouldn’t let me admit any of that. I’m an idiot for pushing you away.” 

“As much as you love me… you mean, you still do?” 

Dean nodded. “Yeah. I never stopped. Hell, even when I wanted to, I still couldn’t.” 

You smiled softly, brushing the tears from your face. “Wow. We’re a couple of morons, huh.” 

“That’s one way to put it.” He shrugged, gently cupping your face in his hand and running his thumb against your cheek - the tentative action making warmth soar through every vein in your body. 

“So, what now?” you asked, not wanting the moment between you to end. 

Dean didn’t pull his hand away, just tucked a strand of loose hair behind your ear. “I’ll loan you the money to give to Bela. I can come with you to the meetup, if you want.” 

“Will you let me call the shots?” you checked, making Dean’s lips quirk in amusement. 

“You’re sounding like a real mobster, sweetheart.” 

“Shut up,” you groaned, playfully swatting his shoulder and making him chuckle.

“I’m being serious, Dean,” you added when his laughter died down. “I have to pay Bela back and make sure Matt will be safe from now on. It’s my fault he’s got himself in this mess.” 

Dean frowned. “Hey, the accident wasn’t your fault. He’s your family, of course he’d want to look out for you. It’s what I would’ve done too.” 

You smiled at the sentiment, finding yourself carding your fingers through his soft hair, lost in this old normality between you, like back when you were together. 

“I know, but you’re used to pissing off the wrong people. Matt isn’t.” 

“That’s real poetic,” Dean laughed. The sight warmed your heart. You’d honestly forgotten how nice it was to see Dean smile, to watch him laugh and feel genuine happiness. 

You’d missed everything about him. Every. Single. Thing. 

“All right,” Dean stepped away, clapping his hands together. “Whatcha say we go and pay Bela a visit? Pinky promise you can call all the shots. I’ll even just sit in the car and wait for you.” 

You raised an eyebrow, watching as he knelt down next to the bed to move the floorboards and get the secret stash of cash hidden beneath. 

“You’re really going to wait in the car?” you questioned, unconvinced. 

Dean grunted as he stretched to reach for the hidden bag, the noises sending your thoughts off into a whole other spiral of memories. If he’d answered your question, you didn’t hear him.

“Gotcha!” he grinned, victorious as he got himself up with the bag in his hand. 

“And yeah, I’ll wait in the car. Scouts honour.” 

“I’m holding you to that, Winchester,” you teased.

“Here’s to new beginnings.” 


End file.
